7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine → HCID 70980161, compound

HRID 81990Notes

Reaction equation

HRID 81990 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH3:22])=[C:12]([N+:17]([O-])=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1.[H][H]>CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH3:22])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 709800257-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine2×HCID 178418361HCID 178418361, compound

Product 1

HCID 70980161HCID 70980161, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine (0.20 g, 0.473 mmol, for preparation see Intermediate 23) was dissolved in EtOAc (80 ml) and hydrogenated using a flow hydrogenator (H-Cube™ settings: full Hydrogen mode, atmospheric pressure, 20° C., 1 ml/min flow rate) to give an orange solution. The eluant was evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)quinoline-3,4-diamine (0.17 g, 0.433 mmol, 91% yield) as an orange gum which was used without further purification. LCMS (formate) Rt 0.66 min, MH+ 393.

Workup

  1. customto give an orange solution
  2. customThe eluant was evaporated in vacuo

Sources & evidence

ORD record
ord-bb00bbcae102421d9e27d936880856c0
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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